


Keep Holding On: Confrontation

by thegreatficmaster



Series: Keep Holding On [2]
Category: Supernatural
Genre: Arguing, Jessica Moore Being an Asshole, M/M, Protective Dean Winchester, Reader-Insert, Sam Winchester Being an Asshole, Shameless Smut, Smut, Sweet Dean Winchester
Language: English
Status: Completed
Published: 2019-08-19
Updated: 2019-08-19
Packaged: 2020-09-07 14:02:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,641
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20310697
Author URL: https://archiveofourown.org/users/thegreatficmaster/pseuds/thegreatficmaster
Summary: After returning home, Y/n sees the true Jess.





	Keep Holding On: Confrontation

Dean was held back by John, struggling against his dad as he tried his hardest to surge forward and beat his brother senseless.

“Dean Winchester! Calm down!”

Mary’s shrill voice stopped Dean in his tracks, knowing he shouldn’t be testing her right now.

John made sure his son wasn’t about to make any move towards Sam, and let him go, standing beside both of them, just in case.

“Sam? Is it true?”

Both Sam and Jess avoided everyone’s eyes, embarrassed and ashamed, and nodded.

“You dated my fucking boyfriend? Then cheated on him? For that?” Dean spat, pointing at Jess and looking at her in disgust.

“Hey! Don’t talk about her like that!“

“Like what? Like she’s trash? A whore? Just like you, I guess!”

Sam had to hold himself back, knowing Dean was taunting him.

“Dean. Stop”.

Dean took a deep breath, running his hand down his face and turned to comfort y/n.

“Y/n?”

Dean looked around the kitchen, realizing he wasn’t in there with them.

“Dean”, Mary pointed to the open back door, Dean realizing he’d gone off on his own.

“Shit!”

He ran out, not caring that he was going to get cold, only caring about finding y/n right now.

“Y/n! Y/n!” he yelled, running out of the yard and into the street, wondering which way to go.

He stared at both ends of the street, knowing it would take forever to get to him.

Dean ran back to the garage, opening it and jumping into the impala.

He drove around frantically, racking his brain, trying to think where y/n could be right now.

He drove to anyone he could think of: neighbours, friends and the local motel. 

Luckily the town was small and there wasn’t really anywhere y/n would’ve gone, but Dean still had no luck finding him.

He continued driving, until the car screeched to a halt.

Dean pushed the door open and ran around the front, running into the little woods and kneeling down in front of y/n, who was sat on a stump just where the woods started.

“Y/n! Baby, what are you doing out here? Hmm?”

Dean rubbed his arms up and down y/n’s shivering form, pulling him closer and holding him tight, needing to warm him up.

“Come on. Let’s get you out of here”.

Dean picked y/n up, carrying him back to the car and lay him across the back, sitting with him and rubbing his cold legs, the slippers soaked wet, his feet cold and freezing, just like the rest of his body.

“You’re freezing. What the hell did you think you were doing? Huh?!” Dean yelled, the fright and concern now turning into anger.

Y/n didn’t say anything, just staring ahead of him.

What was he meant to say? 

That he hated Sam? 

He hated Jess? 

He honestly wished misfortune and sadness upon them? 

Or was he supposed to admit that he was terrified. 

That once the thoughts crossed his mind, that was all he could think about? 

Terrified that Dean would leave him. Leave him to save his relationship with his brother. 

What the hell was he supposed to say?

He had no clue, so he stayed quiet, staring at the back of the front seat, the tears flowing onto the seat, his face warming from where they ran.

They sat there in silence for a few minutes, Dean rubbing y/n’s body through his clothes, warming him up little by little.

Eventually, y/n’s shivering had almost stopped, the slightly damp clothes keeping him wet.

“We need to get you out of these clothes. You might catch a cold”, Dean mumbled, feeling y/n’s sweater, wet and cold.

“It-it’s f-fine. Ju-just take me h-home”, he whispered, his teeth chattering, his voice hoarse.

Dean didn’t listen, pulling off his sweater and t-shirt underneath, pulling y/n’s sweater off as well.

He pulled his boyfriend up, letting y/n straddle him and pulling his chest into his own, their skin touching, the warmth radiating off Dean and onto y/n.

Y/n sighed, just the feeling of Dean making him more at peace, laying his head on Dean’s shoulder and burrowing his face into the crook of Dean’s neck.

Dean couldn’t help but smile. 

He was still angry that y/n would put himself in danger like that. 

But he was just glad he had him here right now, safe in his arms.

Y/n was relieved to be in Dean’s arms, but he couldn’t help but kiss Dean’s neck, the salty taste and the little hairs that he hadn’t shaved yet invading his tongue.

Dean let out a moan, y/n always finding that one spot to make him melt and closed his eyes, his cock already hardening at the thought of y/n, always amazed at how stunning and perfect he was, the way he was tight and warm around his cock.

Y/n felt the bulge beneath him, grinding down, his pants now feeling as though they were two sizes too small, needing to release his cock.

Y/n pulled back, unzipping his pants and attempting to pull them off, the jean material clinging to his legs.

He rolled off Dean and lay back on the seat, Dean helping to pull his pants off, before ridding himself of his own.

They threw their boxers off, both of their cocks now free and standing at attention, precum beaded at the tip.

“No time for anything else. I need to be in you”, Dean panted out, too excited right now to think about anything other than fucking y/n.

Y/n nodded, watching as Dean leaned into the front seat and grabbed a bottle of lube he always kept handy, loving to go and fuck y/n in the impala, especially when it was in public.

He flicked the cap open, pouring a generous amount onto his hand and smearing it all over y/n’s asshole, inserting a single finger and slowly moving it in and out.

Y/n groaned, his head falling against the seat, his mouth hanging open.

“Fuck…Dean…”

He gripped Dean’s face, pulling it down and thrusting his tongue into Dean’s mouth without hesitation, feeling all over and mapping it out, swapping saliva as their tongues glided over each other.

He held Dean close, their chests stuck together, already sweating at this point.

Dean continued stroking y/n’s walls, adding the third finger now and stretching y/n’s ring of muscles, getting him loose enough for his thick cock.

“Get in me, Dean. I need you”.

Dean nodded, his hand exiting y/n and going to his mouth, groaning at the taste as y/n stared at him, his lips wet, eyes hooded and dark with lust.

Dean lined himself up, pressing the tip against y/n’s ass and pushing in slowly, y/n’s ass stretching as Dean filled him up.

None of them said anything, breathing heavily as Dean let y/n adjust to his size, slowly pulling out, before pushing back in.

Y/n let out a few whimpers, loving the feeling, but slightly burning as well.

Dean took it slow, testing it out, before he pulled out softly then thrust back in hard, y/n’s eyes flying open, his hands gripping Dean’s hair and pulling hard, Dean gritting his teeth.

He thrust in and out fast, before he slowed his pace, moving in and out of y/n softly, his cock feeling all of y/n’s walls, kissing his neck, licking his chest and nipples, feeling all of him.

Y/n just let Dean lick his body, loving the feeling of Dean’s full weight on top of him, the way his toned, yet soft stomach, felt against his own.

The way Dean’s arms, which were placed either side of his face, were touching his heated red ears, his hands running through y/n’s hair.

“Let me ride you”.

Dean nodded, his arm snaking underneath y/n’s back and pulling him up, sitting on the seat as y/n straddled him, Dean’s cock inside y/n the entire time.

Y/n stared into Dean’s eyes, cupping his cheeks and leaning forwards, claiming Dean’s lips in a soft kiss.

He pulled back after a while, both men needing to breathe and leaned his forehead against Dean’s, his hands rubbing Dean’s scruffy face, the hairs tickling his fingers, yet feeling soft.

“I love you, Dean”.

Dean smiled, his own hands running down y/n’s back, his thumbs tracing circles on his hips.

“I love you too, y/n. More than you know”.

Y/n nodded, kissing Dean again and began rotating his hips, letting Dean’s cock swirl around inside him, before lifting up slightly, moving up and down on his length.

He bounced on Dean’s cock, letting the tip hit his prostate each time, but knowing that the pace he was going at meant it would take a while to reach their orgasms.

Dean’s mouth fell back to y/n’s neck, sucking on it and leaving bruises, not caring about who would see them. 

All his thoughts were of y/n right now, no one else.

Y/n held Dean’s head close to him, leaning his cheek against Dean’s soft hair and kissing him there.

“Please don’t leave me, Dean”, he whispered, continuing to ride Dean slowly.

Dean moved his head back, staring up into y/n’s watering eyes.

“What?”

Y/n stopped moving, sitting with Dean inside him and looking down at Dean’s chest, wanting to avoid his eyes.

“I-I…” y/n felt the lump in his throat, the thought of Dean leaving him making his stomach lurch.

“**Please don’t let me go**. Don’t-don’t leave me. Don’t choose him over me”, y/n begged, not caring how desperate and pathetic he sounded, or even looked, with the tears that were falling onto Dean’s chest.

Dean began chuckling, pulling y/n into him and stroking his hair.

“Baby, I promise you, no one is more important to me than you. A few years ago, maybe I’d have chosen Sam. But now? He chose her over our family. The things he said? Nothing could make me choose him. Not if it meant I lost you. I mean, I do find it kinda gross knowing he’s been inside you. But you’re all mine now. But-uh-you used protection with him, right?”

Y/n nodded, chuckling and wiping his face.

“Yea, you’re the only guy to cum in me. Don’t worry. And I regret getting with him anyway. I’m not sure what even attracted me to him, but there’s nothing there. I haven’t even thought about him. Especially not since I met you”, y/n admitted.

“Good. Because this is all mine”, he gritted out, suddenly thrusting up into y/n hard, making him yelp and need to balance himself, his palms splayed across Dean’s chest.

“God, Dean. Harder. I need you to cum inside me”.

“Believe me, I’ll cum inside you. I’ll cum so hard, the cum will leak out of you for months”.

Y/n giggled, loving that Dean always got silly during sex.

“Cum in me then. I can leave a trail. Make sure you can find me all the time”, he sassed back, Dean chuckling, y/n able to feel the vibrations on his hands.

“Fine. But don’t blame me when you turn into a snail”.

That set y/n off, giggling the entire time, the car shaking as Dean continued to thrust into him, making jokes, the steamed windows stopping anyone seeing them inside their, the shouts as Dean filled y/n, y/n cumming all over Dean’s chest, being the only disturbance on the empty road.

“You sure you wanna go back in right now?”

Y/n nodded, gripping Dean’s hands, slightly embarrassed that the only thing that was covering him were Dean’s boxers and the sweater Dean was wearing, now only in one layer, instead of the multiple layers he was always in.

“Oh-just take this”, Dean said, grabbing the leather jacket that lay on the workbench in their garage and draping it over y/n, zipping it up, glad that y/n was quite shorter than him so it seemed to cover him.

“Ok, come on. I’m right here”.

Y/n nodded, pushing the door open and walking into the house, shutting the garage door quietly.

_‘You think he found him?’_

_‘He must have, or he’d have called by now’._

Y/n and Dean heard the voices and made their way back to their kitchen, opening the door to find Mary and Jess sat at the table, John behind Mary, rubbing her shoulders, Sam making them some tea.

The creaking made Mary snap her head to the door, her chair scooting back as she ran to y/n, gripping his body tight and squeezing him.

“You had us worried sick!”

“S-sorry. I-I needed some air”, he murmured, staring at the floor, feeling the eyes of the two people he hated most in the world on him.

“It’s ok, son. We just thought maybe something happened”, John commented, moving forward and placing a comforting hand on y/n’s shoulder.

“For someone we just met, you already seem to be part of the family. If Mary’s worried sick, it means you’re a Winchester”.

Y/n smiled, liking the sound of that, everyone missing the little scowl on Jess’ face, having had to work for months to get Mary to warm to her.

“Y-y/n”.

The voice made y/n’s rage return, clenching his jaw.

Just the sound of him made him burn, so he didn’t dare look up.

“W-we didn’t know you were here. Uh…”

Sam had no idea what to say. 

He wanted to apologize. But what would that do?

“We don’t want to hear it. Maybe tomorrow. Right now, I need to get y/n upstairs. So, mom, you and dad can stay in the spare room. Anyone else will have to leave. No trash in the house”.

Y/n bit his cheeks to keep himself from smiling, letting Dean lead him out of the kitchen and up the stairs, hearing Jess hissing at Sam, asking why he didn’t defend her.

They took a quick shower and changed into their pyjamas, Dean in a simple t-shirt and boxers, y/n wearing one of Dean’s larger shirts.

“Thank you”.

“For what?”

Y/n snuggled closer into Dean, placing a kiss on his chest and smiling.

“For defending me. For not letting me go. For choosing me over your brother”.

“I told you, you’re my number one. He’s still my brother, but I haven’t heard from him in years. So there’s no competition.”

Y/n nodded, closing his eyes and letting the scent of Dean surround him, Dean’s arms wrapping around him and lulling him to sleep.

“Boys! Boys, wake up”.

Y/n groaned, peeking through his eyes and seeing a blonde mass above him.

“Come on. We need to talk”.

He groaned, Mary’s voice now recognizable as he rolled over in Dean’s arms, burying his face in the pillow.

“No time for napping! Wake up!”

She pulled the sheets off them, regretting it immediately when she saw her son’s morning wood poking against y/n’s ass.

“Dear lord. I’m so sorry! Just-just come down. Soon”.

She rushed out of the room, hoping she could burn that memory and sat downstairs, looking at Jess and Sam with judgement.

Y/n and Dean came down a few minutes later, dressed in their robes, Dean sitting on the little couch, y/n on his lap.

“Ok. Now that we’re all here, we need to discuss some things”.

Y/n’s eyes flickered to Sam and Jess, sat apart and barely even looking at each other.

“So…of course this news has kind of been sprung on us. I never thought my son was the type, but I guess people change others and bad influences do exist”, Mary said in a clipped tone, knowing Jess was trouble the second she saw her.

“But, this is our Christmas together. Of course, it’s going to be awkward. I know y/n might not want certain people here, but this is the first Christmas we’ve had together in almost seven years. So, I’m begging you, for me, try. It’s only a week”.

Dean looked up at y/n, his eyes silently asking if he was ok with this.

Y/n looked back at Mary and saw the hope on her face and nodded.

“I-I can try”, he answered.

She let out a breath of relief, John pulling her head to his chest and kissing her crown.

“Y/n. Can we talk to you?”

Sam and Jess entered the dining room, Mary and John in the kitchen, Dean out at the store buying more food.

He didn’t answer them, hoping by ignoring them, they’d get the hint and leave.

“Y/n?”

Sam sighed, knowing that he hurt him all those years ago.

“Ok. You don’t have to talk, but just listen. We’re sorry. Ok? All those years ago, we shouldn’t have done it. It was an awful thing to do and it never should have happened. It’s just-we were barely speaking and Jess was there and it just happened. And-we were young. We shouldn’t have done it, but everyone makes mistakes. We never meant to hurt you”.

“Yea. I promise, y/n, we didn’t want that at all. I’m so sorry. I hated myself for so long. You were-you were my best friend. The moment I lost you, I realized everything I’d done was wrong and wished I could take it back. It was the worst thing to do. We both betrayed you. And I’m so sorry for that. I shouldn’t have thrown away our relationship. I regret it so much. I-I’m so sorry”.

They waited, thinking y/n might respond, but were met with silence.

They both turned to leave, when y/n finally spoke up.

“Fuck both of you”.

“W-what?” Jess asked, not used to hearing y/n ever talk to her in this way when they were friends.

“I said, fuck both of you. Fuck your excuses. Fuck your apologies. Fuck your lives. Fuck you!”

“Y/n, we…”

“We what, Sam? What? Honestly, everything out of your filthy ass mouths were just excuses then. We were drifting apart. Yea, that’s probably cos this bitch had her pussy spread for you. I was there. I was there at home waiting for you. You were the one who went to this bitch and fucked her behind my back. And I don’t care what age you were. Everyone knows you shouldn’t cheat. It’s like-a common fact. Then again, you always were a moron. And you?”

He pointed at Jess, the girl staring at him bravely.

“You were supposed to be my best friend. I defended you in school when everyone called you the school slut. I helped with work. I helped when your dad left and your mom went off the rails. I was always there. And you sleep with my boyfriend? No wonder daddy left. A daughter like you? I’d wish you were dead”, he spat, not caring about the hurtful words he was saying.

“Well, that’s your fault. No one told you to be there for me”, she hissed back, Sam just listening, knowing he shouldn’t say anything so he wasn’t yelled at.

“Are you kidding? You’re blaming me for being friends with you? Wow. Wow! I knew you were a crazy bitch. But-fuck! Are you hearing yourself right now?” y/n asked in disbelief.

“Yea, I am. And so what? If you wanted to keep Sam, maybe you should’ve held onto him. Not my fault he came crawling to me”.

“You fucked him that time I was in hospital. Sam told me that was the first time. How the hell was that my fault?”

“Well, if you didn’t take him in the first place, I wouldn’t have had to steal him off you”.

Y/n just stared at her. 

How the hell was he friends with this girl in the first place? 

Why did he never see the vile, putrid person she was for all those years?

“You really are crazy. Aren’t you?”

“Hey!”

Everyone looked to the doorway, Dean standing there, John and Mary rushing out of the kitchen.

“What’s going on?”

“N-nothing. We were just talking. That’s all”, y/n assured Mary, not wanting to let her down.

She looked at Sam and Jess, both smiling back at her.

“Ok. Well, Jess, help me in the kitchen”.

The girl nodded, smiling at y/n triumphantly and walking away, John leaving with both women.

Dean took y/n into his arms and held him, kissing his temple.

“You ok?”

Y/n nodded, just pissed that he had to deal with that crazy bitch.

“Y/n. I’m so sorry. She shouldn’t have said any of that. It’s just the horm…”

Dean held his hand up, his brother shutting his mouth and looking at them.

“Don’t! We don’t wanna hear it. Once this week is over, take Jess and get out”.

Dean didn’t wait for a response, leading y/n out of the room and into the hallway.

“You really ok?”

Y/n smiled at Dean and kissed him softly.

“I promise, I’m fine. It’s just this week anyway. Once it’s over, I’ll be fine”.

Dean nodded, holding y/n in his arms and rocking him back and forth, not able to wait until Christmas day, Mary having helped plan the perfect engagement for them both, wanting to make y/n his husband as soon as possible. 

Sam watched from the corner, knowing he gave up the best thing he ever had, regretting cheating on y/n.

Especially now that y/n belonged to his brother.


End file.
